Method for preparing polyolefins containing vinylidine end groups using azole compounds

Inactive Publication Date: 2007-07-05
CHEVRON ORONITE CO LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

[0017] The contacting step is conducted under suitable conditions to enable the quenching agent to interact with the reactive chain end of the polyolefin and facilitate the removal of a proton from the reactive chain end, thereby forming the vinylidene end group. Thus, selecting suitable quenching reaction system conditions (temperature, Le

Problems solved by technology

Exclusive production of the exo-olefin isomer has not been pre

Method used

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  • Method for preparing polyolefins containing vinylidine end groups using azole compounds
  • Method for preparing polyolefins containing vinylidine end groups using azole compounds
  • Method for preparing polyolefins containing vinylidine end groups using azole compounds

Examples

Experimental program
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Example

Example 1

Preparation of Polyisobutylene Using a Mono-functional Initiator and 2-phenylbenzoxazole

[0111] A four-neck 250 milliliter round-bottom flask was equipped with an overhead mechanical stirrer and platinum resistance thermometer. This assembly was immersed into a heptane bath at −60° C. under dry nitrogen gas in a substantially inert atmosphere glovebox. The flask was then charged with the following reactants:

[0112] 108 milliliters hexane equilibrated at −60° C.,

[0113] 72 milliliters methylchloride equilibrated at −60° C.,

[0114] 0.48 milliliters 2-chloro-2,4,4-trimethylpentane equilibrated at room temperature,

[0115] 0.23 milliliters 2,6-dimethylpyridine equilibrated at room temperature, and

[0116] 16.4 milliliters of isobutylene equilibrated at −60° C.

[0117] Then, the contents of the round-bottom flask were equilibrated at −60° C.

[0118] With continued stirring, next 1.82 milliliters titanium tetrachloride was charged to the flask. The reaction was allowed to proceed 12...

Example

[0120] Examples 2-5 were conducted according to the procedure described above in Example I except that other quenching agents were charged to the quasiliving polymerization instead of 2-phenylbenzoxazole. Additionally, examples 4 and 5 were conducted at −40° C.; Control B represents the final comparative baseline for the reactions conducted at −40° C. The reactant quantities for Examples 1-5 are listed in Table 1.

Comparative Examples A-J

[0121] Polybutene was prepared according to the procedure described in Example 1 above but, various quenching agents other than 2-phenylbenzoxazole were utilized. The comparative examples represent cyclic, aromatic quenching agents containing both nitrogen and another heteroatom within the ring which did not yield more vinylidene PIB than Control A at −60° C. or Control B at −40° C.

[0122] The reactant quantities for comparative examples A-J are listed in Table 1. TABLE I2,6-TotalTotalDimethylQuenchingReactionDiluentInitiatorpyridineIsobutyleneTiC...

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Abstract

Disclosed is a method for preparing polyolefins containing vinylidine end groups from quasiliving carbocationically terminated polyolefin polymers by contacting the quasiliving carbocationically terminated polymer with a suitable azole quenching agent and substituted derivatives thereof.

Description

FIELD OF THE INVENTION [0001] The present invention is directed to a method for preparing polyolefins having enriched vinylidine end groups. More particularly, the present invention is directed to preparing polyolefins containing vinylidine end groups from quasiliving carbocationically terminated polyolefin polymers by contacting the quasiliving carbocationically terminated polymer with quenching agent selected from suitable azole compounds and substituted derivatives thereof. BACKGROUND OF THE INVENTION [0002] Linear polyolefins made using a mono-functional initiator containing a single “exo-olefin”, “1,1-di-substituted” olefin, or “methylvinylidene,” end group are useful precursors for the preparation of polymers containing specific functional end groups. Polymers made using multi-functional initiators would have multiple exo-olefinic end groups. Polymers containing specific end groups are useful as lubricating oil additives. One example of a functionalized polymer containing hete...

Claims

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Application Information

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IPC IPC(8): C08F297/02
CPCC08F110/10C08F2810/40C08F2810/30C08F8/00C08F4/16C08F2/38C08F4/00
Inventor STOKES, CASEY D.STOREY, ROBSON F.
Owner CHEVRON ORONITE CO LLC
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